Phenylpropene

Allylbenzene parent structure

Phenylpropenes, propenylphenols, alkenylbenzenes or allylbenzenes are a class of phenylpropanoids in which a benzene ring has an allyl group attached to it. Phenylpropenes have been used as a precursors for a variety of effective insecticides.[1]

Safrole, a phenylpropene found in sassafras

Flavor or toxin?

Dosage determines concern: There is long standing and wide use as flavors at doses low enough to be insignificant, but high doses as in medicinal use can be a concern. Readily metabolized to reactive carcinogens which are also rapidly metabolized to safe compounds that are excreted. So there is a small window of time when it goes from flavor to toxin to safe.

Alkenylbenzenes at high dose can be activated metabolically (by P450, sulfotransferase) to reactive intermediates that bind DNA, but are also rapidly converted to less toxic dihydrodiol or glutathione conjugates, so there is a small window of time when such compounds go from flavor to toxin to safe. [2]

The phenylpropenes, including eugenol, chavicol, safrole and estragole, are derived from the monolignols. These compounds are the primary constituents of various essential oils.

See also

References

  1. ↑ Fujita, Harushige and Yamashita, Masataro (1973). "The Methylenation of Several Allylbenzene-1,2-diol Derivatives in Aprotic Polar Solvents". Bulletin of the Chemical Society of Japan 46 (11): 3553–3554. doi:10.1246/bcsj.46.3553. Retrieved 27 December 2013.
  2. ↑ Guenthner, Toxicology 160:46 2001


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